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Connecting team and strategic planning in agile organizations

Connecting team and strategic planning in agile organizations
Within the past 4 month, I’ve been working within an IT Operation division in a financial institution in Montreal, particularly with the people who work to support the production environments for the rest of the IT organization.
It has been a challenging and interesting experience, where I have been able to test, once again, my hypothesis about how crucial is to keep the business connected with IT, in order to help modern organizations succeed.
Observations
What I have noticed, is that not matter the type of work a team does, there is always a need to have visibility over the following areas:

Things that are coming up next (upcoming iteration for example)

What is in the pipeline (Medium Term – at least the upcoming 3 months)

How things are progressing at every level (team and organizational level)

Challenges
Everyone has its way to keep things visible, but I have found that:

Keeping teams in sync with what the business wants at a fast pace, is extremely difficult and hard to keep on doing it.

Keeping stakeholders informed, regarding what is next on the team’s pipeline, could be extremely costly and demanding for the team and Product Owner/Managers specifically.

Keeping managers informed to enable them to make the right decisions and support their teams at what they need the most, is complex and sometimes impossible to accomplish.

How do I do to help teams and organizations with bridging the gap?
It’s all wrap up in the following picture:
Put into words, here the activities that I do, to help with connecting both sides:

Still a work in progress
Here is what I’ve found have been more challenging, when implementing the framework above:

Keep PO’s and stakeholder interested into talk periodically.

Keep PO’s bringing Team’s Road map to the team and stay open to be challenged.

Keep track of goal progression when there are more than 2 teams involved.

Move away from the physical version of the team’s road map towards an electronic version that could be shared across the organization.

What do you think?
All I have mentioned within this article is based on my own experiences, and even if it seems to work (I have used with 10 teams from different domains, size and cultures), I would love to hear from you, how do you do it, so help me out by sharing your experiences with me and I would love to give it a try.
Thank you for your help and for being there to make my journey a better one.
References
Jesus Mendez, Forming Agile Teams (6) Levels of Planning + Experiment
Black Swan Farming, Qualitative Cost of Delay